Born in Gander and raised in Riverhead, Harbour Grace, and Bay Roberts, Cleary graduated from the journalism program at the Stephenville campus of the College of the North Atlantic in 1989. On May 2, 2011, Cleary was elected to the House of Commons in the 2011 election.

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As a journalist, Cleary covered most of the major events in Newfoundland and Labrador over the past two decades. He was fisheries reporter for The Telegram in 1992 when the moratorium was first introduced on northern cod. He also worked as a political and investigative reporter and has won numerous journalism awards and accolades throughout his career.

Cleary was the editor-in-chief of The Independent newspaper and was known for his outspoken and controversial articles. As a journalist Cleary was critical of the NDP and had advocated for Newfoundland and Labrador separating from Canada.[1] When The Independent went out of business he went on to host Nightline, a VOCM radio call in program. Cleary also worked for The Newfoundland Herald, NTV, and Time Magazine.

Cleary first entered politics when he became the New Democratic Party (NDP) candidate in the riding of St. John's South—Mount Pearl in the October 2008 federal election. His candidacy led to some controversy for him and NDP leader Jack Layton for comments Cleary had written only a couple of years before when he was a journalist. Cleary had referred to NDP supporters as a "small pocket of aging granolas and artsy-fartsies" and that they were "a mainstream party that wouldn't win an election if Jackie Layton was given a 100-seat head start."[1][2] Despite his late entrance into the campaign and his previous comments he still managed to place a strong second in the riding.[3]

On September 17, 2009, the New Democrats nominated Cleary as their candidate in St. John's South-Mount Pearl for the next federal election.[4] In October 2010, Cleary announced that he would withdraw his candidacy. He stated that being a political candidate has created a conflict with his journalism work and that he wished to continue with his journalism career. He also noted that he had severed all ties with the NDP.[5] However, in March 2011 with the announcement of a federal election, Cleary said he would return to run for the NDP again.[6] On May 2, Cleary defeated Liberal Siobhán Coady receiving 18,332 votes to Coady's 10,670.[7]